Totally Home
apartment, Pittsfield
This centrally located apartment in Berkshire County offers easy access to Tanglewood, located approximately 6 miles away, and other regional attractions.
This two-bedroom, one-bathroom residence accommodates two guests and features a private second-floor porch, access to backyard gardens, and dedicated workspaces, ideal for summer stays with flexible access to New York and Boston.
This two-bedroom, one-bathroom residence accommodates two guests and features a private second-floor porch, access to backyard gardens, and dedicated workspaces, ideal for summer stays with flexible access to New York and Boston.
Cozy Bungalow In Se Pittsfield
apartment, Pittsfield
This Pittsfield apartment is located just 5 minutes from Bousquet Ski Mountain and 20 minutes from Jiminy Peak, offering easy access to outdoor activities in the Berkshires. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The rental is a single-floor home with space for 5 guests. It features a fully equipped kitchen, a private garden, a deck and an enclosed porch, and a grill for cookouts, making it ideal for entertaining friends and family.
The rental is a single-floor home with space for 5 guests. It features a fully equipped kitchen, a private garden, a deck and an enclosed porch, and a grill for cookouts, making it ideal for entertaining friends and family.
Willowbrook: A Sun Filled, Mid-century Modern Home
apartment, Pittsfield
This 7-bedroom home is located in Dalton, just minutes from Pittsfield, Massachusetts, offering easy access to the town's attractions and charming downtown. The apartment has received excellent ratings for location, cleanliness, and user experience, making it an ideal choice for travelers.
This spacious rental can accommodate up to 14 guests, with multiple bedrooms featuring ensuite bathrooms for privacy. Enjoy a fully equipped kitchen, two living rooms, a large desk, a private garden, and parking.
This spacious rental can accommodate up to 14 guests, with multiple bedrooms featuring ensuite bathrooms for privacy. Enjoy a fully equipped kitchen, two living rooms, a large desk, a private garden, and parking.
Your Berkshires Home Base
apartment, Dalton
This Dalton, Massachusetts family-friendly apartment rental is conveniently located near Tanglewood and Mass MoCA, offering easy access to Berkshire cultural attractions.
The three-bedroom, two-bathroom dwelling sleeps six, includes a dedicated office, a full kitchen with dishwasher, and provides access to a garden and parking.
The three-bedroom, two-bathroom dwelling sleeps six, includes a dedicated office, a full kitchen with dishwasher, and provides access to a garden and parking.
Solomon Ely Homestead - Charming Pittsfield Stay
apartment, Pittsfield
This Pittsfield vacation home offers a central location, within a 10-minute walk of the Berkshire Athenaeum, Colonial Theatre, and Berkshire Museum, and less than a mile from the Barrington Stage Company and the Housatonic River.
This four-bedroom, two-bathroom house sleeps seven and features a fully equipped kitchen with a refrigerator, microwave, dishwasher, and a coffee/tea maker, plus a Smart TV, in-unit laundry, and on-site parking.
This four-bedroom, two-bathroom house sleeps seven and features a fully equipped kitchen with a refrigerator, microwave, dishwasher, and a coffee/tea maker, plus a Smart TV, in-unit laundry, and on-site parking.
Spacious Historic Home In The Berkshires!
cottage, Pittsfield
This Pittsfield cottage boasts a prime location, within a 10-minute walk of the Colonial Theatre, Berkshire Athenaeum, and Berkshire Museum, and less than a mile from the Housatonic River and Barrington Stage Company.
This pet-friendly vacation home features two bathrooms, a fully equipped kitchen with microwave and dishwasher, a private balcony, free Wi-Fi, and free self-parking, plus a fireplace and air conditioning for added comfort.
This pet-friendly vacation home features two bathrooms, a fully equipped kitchen with microwave and dishwasher, a private balcony, free Wi-Fi, and free self-parking, plus a fireplace and air conditioning for added comfort.
Dancing Horse Lodge
apartment, Pittsfield
This vacation rental is located in the mountains, just a short drive from Pittsfield's cultural attractions like the Colonial Theater, Berkshire Museum, and Housatonic River. The house has earned excellent ratings for its cleanliness, location, and overall experience.
The home has 3 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. Enjoy amenities like a fully equipped kitchen, a garden, and a relaxing mountain setting.
The home has 3 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. Enjoy amenities like a fully equipped kitchen, a garden, and a relaxing mountain setting.
Marie's Place
apartment, Pittsfield
This apartment is located in Pittsfield, just a short drive from the city's cultural attractions like the Berkshire Museum, Colonial Theater, and Barrington Stage Company. It has excellent user, location, and cleanliness ratings, making it a great choice for travelers. The apartment is fully furnished and comfortably accommodates up to four guests. You'll enjoy convenient on-site laundry facilities, off-street parking, and access to the yard and parking area, making your stay hassle-free.
Beautiful Lake-view Getaway!
apartment, Pittsfield
This Pittsfield lakeside rental boasts stunning lake views and easy access to Berkshire attractions, offering a perfect base for exploring the region.
This two-bedroom, one-bathroom house sleeps four, features a full kitchen with dishwasher, a jacuzzi, a fire pit, and a patio—ideal for year-round getaways, from summer lake recreation to winter skiing.
This two-bedroom, one-bathroom house sleeps four, features a full kitchen with dishwasher, a jacuzzi, a fire pit, and a patio—ideal for year-round getaways, from summer lake recreation to winter skiing.
Lakefront Home In The Heart Of The Berkshires
apartment, Pittsfield
This lakefront home is located near Pittsfield, Massachusetts, within a 20-minute drive of Jiminy Peak ski resort and Tanglewood, and a 10-minute drive from the Berkshire Museum. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The spacious 4-bedroom, 4-bathroom dwelling offers ample room for up to 10 guests. Enjoy stunning lake views, a private balcony, multiple living areas, three decks, a patio with a fire pit, and access to a garden, a Jacuzzi, and parking.
The spacious 4-bedroom, 4-bathroom dwelling offers ample room for up to 10 guests. Enjoy stunning lake views, a private balcony, multiple living areas, three decks, a patio with a fire pit, and access to a garden, a Jacuzzi, and parking.
Cozy Pittsfield Gem W/ Deck, Gazebo & Fireplace!
apartment, Pittsfield
This 3-bedroom, 3-bathroom Pittsfield apartment offers convenient access to outdoor recreation, located 8 miles from Bousquet Mountain Ski Area and 12 miles from Jiminy Peak Mountain Resort, with Ashuwillticook Rail Trail just 1 mile away and Pittsfield State Forest 8 miles distant.
This family-friendly residence accommodates up to 10 guests with a fully equipped kitchen, fireplace, Smart TV, in-unit washer/dryer, and outdoor spaces including a deck, balcony, and gazebo, plus a main-level bedroom and bathroom ideal for guests with mobility considerations.
This family-friendly residence accommodates up to 10 guests with a fully equipped kitchen, fireplace, Smart TV, in-unit washer/dryer, and outdoor spaces including a deck, balcony, and gazebo, plus a main-level bedroom and bathroom ideal for guests with mobility considerations.
Cantabile Life In The Berkshires
apartment, Pittsfield
This apartment is located in a quiet, friendly neighborhood in Pittsfield, just minutes from several lakes, mountains, and attractions like Tanglewood and Bousquet Ski Area. It boasts excellent ratings for location, cleanliness, and user satisfaction.
The rental offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the spacious living areas, well-equipped kitchen, and outdoor space, plus family-friendly amenities like games, a piano, and child-friendly equipment.
The rental offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the spacious living areas, well-equipped kitchen, and outdoor space, plus family-friendly amenities like games, a piano, and child-friendly equipment.
